Hydrochloric Acid → HCID 24850409, compound

HRID 2075209Notes

Reaction equation

HRID 2075209 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:23][N:24]2[CH2:27][CH:26]([C:28]([O:30]CC)=[O:29])[CH2:25]2)[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[CH:13][C:11]=2[CH:12]=1.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:23][N:24]2[CH2:25][CH:26]([C:28]([OH:30])=[O:29])[CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[CH:13][C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58415291HCID 58415291, compound

Product 1

HCID 24850409HCID 24850409, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
24 °C

Procedure

A mixture of ethyl 1-((3-fluoro-4-(5-(thiazol-2-ylmethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate (290 mg, 644 μmol) in THF (5 mL) was treated with a solution of LiOH (27 mg) in H2O (2 mL) and stirred at 24° C., neutralized with 0.1M aqueous HCl, and concentrated. The resulting solids were collected by filtration and purified by RP-HPLC to give 1-((3-fluoro-4-(5-(thiazol-2-ylmethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a white solid [hS1P1 EC50=76 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.93-7.91 (m, 1H), 7.73 (s, 1H), 7.66-7.58 (m, 3H), 7.32-7.28 (m, 4H), 4.44 (s, 2H), 3.65 (br. s, 2H), 3.46 (br. s, 2H), 3.30-3.26 (m, 3H). MS (ESI) m/z: Calculated: 422.1; Observed: 423.2 (M++1).

Workup

  1. concentrationconcentrated
  2. filtrationThe resulting solids were collected by filtration
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-6dae00560fa845baa54e8f94c1c520e6
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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